Diels-Alder reaction of (2,4,6-trialkylphenyl)phospholes withN-phenylmaleimide

Keglevich, György; Trecska, Mónika; Dajka, Beáta; Pete, Béla; Dobó, András; Tőke, Lásʐló

doi:10.1002/1098-1071(2000)11:4<271::aid-hc5>3.0.co;2-t

Cited by 17 publications

(1 citation statement)

References 12 publications

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“…The early results have been summarised in Reviews on Heteroatom Chemistry [17] and Trends in Organic Chemistry [18].…”

Section: Introductionmentioning

confidence: 99%

6-Membered P-Heterocycles: 1,2-Dihydro-, 1,2,3,6-Tetrahydro- and 1,2,3,4,5,6-Hexahydrophosphinine 1-Oxides

Keglevich

2006

COC

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The members of a logically built P-heterocyclic family are discussed systematically to show a dynamically developing discipline of organophosphorus chemistry. Dichlorocyclopropanation of 2,5-dihydro-1H-phosphole oxides led to 3-phosphabicyclo[3.1.0]hexane 3-oxides that were useful intermediates for the synthesis of ring expanded products, such as 1,2-dihydrophosphinine oxides and 3-alkoxy-1,2,3,6-tetrahydrophosphinine oxides. Catalytic hydrogenation of 1,2-dihydrophosphinine oxides gave 1,2,3,4,5,6-hexahydrophosphinine oxides. Selective reduction of the , -doublebond of 1,2-dihydrophosphinine oxides via hydroboration led to 1,2,3,6-tetrahydrophosphinine oxides. Michael addition of >P(O)H species to the electron-poor double-bond of 1,2-dihydrophosphinine oxides afforded 1,2,3,6-tetrahydrophosphinine oxides with exocyclic P-function in position 3. Hydrogenation of these P-heterocycles led to the corresponding hexahydrophosphinine oxides. Stereostructure and conformation of the tetra-and hexahydrophosphinine oxides were elucidated by stereospecific NMR couplings and/or quantum chemical calculations. After deoxygenation, some of the above P-heterocycles were suitable P-ligands in transition metal complexes. The 1,2-dihydrophosphinine oxides were also useful in the synthesis of aromatic phosphinines, phosphepine derivatives and phosphabicyclo[2.2.2]octene oxides, as well as hetrocyclic -oxophosphoranes.

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“…The early results have been summarised in Reviews on Heteroatom Chemistry [17] and Trends in Organic Chemistry [18].…”

Section: Introductionmentioning

confidence: 99%

6-Membered P-Heterocycles: 1,2-Dihydro-, 1,2,3,6-Tetrahydro- and 1,2,3,4,5,6-Hexahydrophosphinine 1-Oxides

Keglevich

2006

COC

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Study on the uv light-mediated fragmentation of 7-(2,4,6-trialkylphenyl-)7-phosphanorbornene 7-oxides in alcohols: New evidences on the mechanism

et al. 2001

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Heterobimetallic Gold/Ruthenium Complexes Synthesized via Post‐functionalization and Applied in Dual Photoredox Gold Catalysis

Bayer

Birenheide

Krämer

et al. 2022

Chemistry A European J

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The synthesis of heterobimetallic AuI/RuII complexes of the general formula syn‐ and anti‐[{AuCl}(L1∩L2){Ru(bpy)2}][PF6]2 is reported. The ditopic bridging ligand L1∩L2 refers to a P,N hybrid ligand composed of phosphine and bipyridine substructures, which was obtained via a post‐functionalization strategy based on Diels‐Alder reaction between a phosphole and a maleimide moiety. It was found that the stereochemistry at the phosphorus atom of the resulting 7‐phosphanorbornene backbone can be controlled by executing the metal coordination and the cycloaddition reaction in a different order. All precursors, as well as the mono‐ and multimetallic complexes, were isolated and fully characterized by various spectroscopic methods such as NMR, IR, and UV‐vis spectroscopy as well as cyclic voltammetry. Photophysical measurements show efficient phosphorescence for the investigated monometallic complex anti‐[(L1∩L2){Ru(bpy)2}][PF6]2 and the bimetallic analogue syn‐[{AuCl}(L1∩L2){Ru(bpy)2}][PF6]2, thus indicating a small influence of the {AuCl} fragment on the photoluminescence properties. The heterobimetallic AuI/RuII complexes syn‐ and anti‐[{AuCl}(L1∩L2){Ru(bpy)2}][PF6]2 are both active catalysts in the P‐arylation of aryldiazonium salts promoted by visible light with H‐phosphonate affording arylphosphonates in yields of up to 91 %. Both dinuclear complexes outperform their monometallic counterparts.

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Diels-Alder reaction of (2,4,6-trialkylphenyl)phospholes withN-phenylmaleimide

Cited by 17 publications

References 12 publications

6-Membered P-Heterocycles: 1,2-Dihydro-, 1,2,3,6-Tetrahydro- and 1,2,3,4,5,6-Hexahydrophosphinine 1-Oxides

6-Membered P-Heterocycles: 1,2-Dihydro-, 1,2,3,6-Tetrahydro- and 1,2,3,4,5,6-Hexahydrophosphinine 1-Oxides

Study on the uv light-mediated fragmentation of 7-(2,4,6-trialkylphenyl-)7-phosphanorbornene 7-oxides in alcohols: New evidences on the mechanism

Heterobimetallic Gold/Ruthenium Complexes Synthesized via Post‐functionalization and Applied in Dual Photoredox Gold Catalysis

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